What Bernie Sanders needs to learn from Hillary Clinton, and vice versa

A steady dripof comments just before the Iowa caucuses has left little doubt: Many former Obama aides consider Hillary Clinton his natural heir. One former staffer put it pretty directly, saying that Bernie Sanders’s campaign “resembles Howard Dean’s a lot more than it resembles Barack Obama’s.”

It was a clear shorthand for “insurgent who lost” — fair enough. Obama’s the insurgent who won, right?

But that isn’t really the whole story. The Obama organization’s strength eight years ago came from its unlikely and somehow functional mix of insurgents and insiders. This time, the two leading Democrats are each succeeding in only half of that equation — and that’s a problem they will both need to solve to have the best chance at winning a general election.

(Two disclaimers at this point. One: I ran Obama’s digital efforts in 2008 and 2012, but I don’t personally have a candidate in this race. Two: The company I lead, Blue State Digital, has done work for all three Democratic presidential campaigns and the Democratic National Committee this cycle.)

Obama’s 2008 campaign achieved an incredibly difficult balance, making an orderly organization out of the pragmatic and the pissed-off alike. Many senior staffers were operatives who’d worked in Congress or for previous Democratic presidential bids, but a huge portion of the wider team, especially in the field and digital operations, had little previous campaign experience, if they had any. Obama himself reflected these two sides: The measured constitutional law professor was also the community organizer who’d opposed “a dumb war ” in Iraq.

That a grass-roots movement propelled Obama in 2008 is well-known: A huge share of our volunteers and small-dollar donors were engaging with the political process deeply for the very first time. But that campaign redefined modern election tactics not only by raising a massive grass-roots insurgency but by playing the inside game well.

The insiders were crucial in building the case for Obama with outreach to elected officials, big donors and superdelegate types who could help him secure the Democratic nomination and the influence of the mainstream media. The finance team matched Clinton and outpaced John McCain in 2008, and then Mitt Romney in 2012, dollar for dollar in large contributions. Those insiders built a kind of scaffolding, and the insurgent grass roots stretched to bring in more small-dollar donations than any other campaign in history and did the hard work at the doors, on the phones and in the community that provided our margin of victory. That inside game is the sort of campaign that Clinton has excelled at, especially in this cycle, and it’s been one of Sanders’s biggest weaknesses up to now.

But one of the underappreciated consequences of those Obama campaigns, which we’re seeing play out in this primary and will be felt for years to come, has been the modernization of mass mobilization in the Democratic Party. Thousands of staffers and volunteers got the training and seasoning that come with being part of a big, broad grass-roots effort.

This means there’s a new default level of sophistication for a Democratic presidential campaign. Both the Clinton and Sanders teams inherited an ingrained culture of constant testing and data-driven optimization that shapes every ad, every email, every call script for a volunteer and every list of voters they call. And both campaigns have built their organizing efforts on the foundation of tech and data infrastructure at the Democratic National Committee that first came together in the 2008 cycle.

This modernization of movement-building also means that the potency of an insurgent-led campaign has grown — by a lot. In a previous era, a candidate like Sanders might have been deprived of the scarce talent or limited party infrastructure needed to mount an enterprise-level campaign. But Sanders has been able to make use of the wide talent pool and the specific tech cultivated by Obama, and he’s now surpassed the pace of grass-roots fundraising that the Obama campaign set in 2008 and 2012, with more than 2.5 million individual contributions before the Iowa caucuses. (Obama, by the end of 2011, had 2.2 million.)

That’s not because he’s a more compelling candidate than Obama or because he’s got a better shot of winning than Obama did at this point in the 2008 race. But the people doing the organizing and small-donor fundraising, and the technology platforms they use, trace their roots to the insurgent branch of the Obama campaign — and in some cases even to Dean’s campaign and his tenure as chairman at the DNC.

Perhaps even more important than skills and software, the insurgents have been emboldened with the audacity to think they can win. And it’s clear that, whether you support him or not, Sanders’s campaign is the home of the prevailing grass-roots energy in this race. The most recent financial reports, for the period that ended in October, showed that the amount Clinton raised from donors giving less than $200 decreased from $8 million to $5.2 million, while Sanders’s low-dollar take nearly doubled, from $10.4 million to $20.2 million. Clinton raised barely a quarter of the amount from grass-roots donors that Sanders did. Whatever the ultimate result, that shows the Sanders campaign has accomplished extraordinary things in volunteer mobilization and small-donor fundraising, period.

Those accomplishments are all the more remarkable for just how isolated from elites Sanders’s campaign is. One tally of endorsements by various elected officials puts Clinton ahead of Sanders 458 to 2. Even more than Dean in 2004, Sanders is running a true outsider bid. Yes, there was an outpouring of grass-roots support for Dean (I worked on that campaign, too), but he also had an inside game that people tend to forget. Heading into Iowa, he had endorsements from Al Gore, former Texas governor Ann Richards, Sen. Tom Harkin of Iowa, and big unions such as the Service Employees International Union and the American Federation of State, County and Municipal Employees. The campaign just blew it, failing to turn either all that insider cred or its insurgent energy into a functioning organization.

Obama proved there’s no reason to conflate “insurgent” with “disorganized.” But Clinton is actually playing the inside game now better than she did eight years ago: Her total dominance among party leadership far exceeds her 2008 position or even Gore’s over Bill Bradley in 2000. Whether you support her or not, she and her team set out to build — and have built — the kind of base that, if not for the new durability of an insurgency like Sanders’s, would have cleared the field and made for a formidable, unified front in November. A successful general-election campaign requires that kind of skill and political organization. Without it, even the largest-scale insurgent campaign won’t be sufficient to marshal a major political party to victory.

No matter who wins, though, this primary season has shown — even before the voting begins — that our eventual nominee will need to figure out how their organization can replicate what the other candidate has done so well. If Clinton prevails, she’ll need to find a way to build the grass-roots side of her campaign and encourage the many people who are legitimately excited about her candidacy to be more actively engaged in it. If Sanders wins, he’ll need to pay far more attention to traditional politics than he’s done so far, in order to leverage the institutional support that the Democratic Party apparatus can provide its nominee.

The winner will be tempted to view victory as a validation of the insider-friendly or insurgent-led approach. But they will need to grapple with the reality that the opponent they’ve just defeated will, nevertheless, have accomplished something they didn’t.